Superacid catalyzed preparation of resorcinol from meta-isopropylphenol

Abstract

Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic superacids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic superacid of one to eighteen carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.

I claim: 
     
       1. A process of preparing substantially pure meta-isopropylphenol which comprises propylating phenol with: (a) propylene,   (b) an isopropyl halide,   (c) an isopropyl alcohol,   (d) di isopropylbenzene,   (e) tri isopropylbenzene,   (f) di isopropylphenol, or   (g) tri isopropylphenol, in the presence of a combination catalyst of:     (1) an excess of anhydrous hydrogen fluoride and a Lewis acid fluoride, or   (2) an excess of anhydrous hydrogen fluoride and a perfluorinated alkanesulfonic superacid of one to eighteen carbon atoms, at a temperature sufficient to produce substantially pure meta-isopropylphenol.     
     
     
       2. The process of claim 1 in which the Lewis acid fluoride catalyst is boron trifluoride, phosphorous pentafluoride, arsenic pentafluoride, antimony pentafluoride, tantalum pentafluoride or niobium pentafluoride. 
     
     
       3. A process of preparing substantially pure meta-isopropylphenol which comprises reacting a mixture of phenol and diisopropylphenol in the presence of a combination catalyst of: (1) an excess of anhydrous hydrogen fluoride and a Lewis acid fluoride, or   (2) a excess of anhydrous hydrogen fluoride and a perfluorinated alkanesulfonic superacid of one to eighteen carbon atoms, at a temperature sufficient to produce substantially pure meta-isopropylphenol.     
     
     
       4. The process of claim 3 in which the Lewis acid fluoride catalyst is boron trifluoride, phosphorous pentafluoride, arsenic pentafluoride, antimony pentafluoride, tantalum pentafluoride or niobium pentafluoride. 
     
     
       5. The process of one of claims 1, 2, 3, or 4 carried out at temperatures between about -50° and 200° C.